Toluene → HCID 15442724, compound

HRID 479006Notes

Reaction equation

HRID 479006 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([C@@H:15]([OH:18])[CH2:16][OH:17])[CH:12]=[CH:13][CH:14]=1.C1(C)C=C[C:22]([S:25](Cl)(=[O:27])=[O:26])=CC=1>N1C=CC=CC=1>[CH3:22][S:25]([O:17][CH2:16][C@@H:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[CH:10]=1)[OH:18])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 9815352(R)-1-(3-Chlorophenyl)-1,2-ethanediol

Product 1

HCID 15442724HCID 15442724, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into toluene (30 ml) were added (R)-2-(3-chlorophenyl)-2-hydroxyethanol obtained in 1) above (7 g), pyridine (8.0 g) and further, under ice-cooling and dropwise, p-toluenesulfonyl chloride (9.3 g), and then the resulting mixture was stirred at the same temperature for 24 hours. The solid thus precipitated was filtered off, the filtrate was concentrated, and the residue was dissolved in toluene (40 ml) and then washed with dilute hydrochloric acid. The organic layer was collected by layer separation, washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was filtered off, the solvent was distilled off under reduced pressure, and the residue was recrystallized from diethyl ether and hexane to obtain a colorless oily compound mentioned above (10.6 g, 80.0%).

Workup

  1. temperaturefurther, under ice-cooling
  2. customThe solid thus precipitated
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated
  5. dissolutionthe residue was dissolved in toluene (40 ml)
  6. washwashed with dilute hydrochloric acid
  7. customThe organic layer was collected by layer separation
  8. washwashed with a saturated aqueous sodium chloride solution
  9. dry with materialdried with anhydrous magnesium sulfate
  10. filtrationThe desiccant was filtered off
  11. distillationthe solvent was distilled off under reduced pressure
  12. customthe residue was recrystallized from diethyl ether and hexane
  13. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-24f20d1e37ad4aeab9522802b6e76222
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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